US4388469AExpiredUtility

Diphenylalkanoether and diphenylalkanone oximeether derivatives

48
Assignee: SUMITOMO CHEMICAL COPriority: Apr 2, 1979Filed: Apr 2, 1980Granted: Jun 14, 1983
Est. expiryApr 2, 1999(expired)· nominal 20-yr term from priority
Inventors:Keiichi OnoHajime KawakamiJunki Katsube
C07D 213/30C07D 333/16C07D 307/42C07D 295/088
48
PatentIndex Score
1
Cited by
13
References
15
Claims

Abstract

Diphenylalkanoether and diphenylalkanone oxime-ether derivatives of the formula: ##STR1## wherein R 1 and R 2 are each independently an aryl group optionally substituted with 1 to 3 substituents selected from the group consisting of halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, nitro, cyano, di(C 1 -C 4 )alkylamino, amino, benzyloxy, hydroxyl, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 alkanoylamino, C 1 -C 4 alkylamino and N-(C 1 -C 4 )alkyl-N-(C 1 -C 4 )alkanoylamino, Z 1 is a group of the formula: ##STR2## (wherein R 3 and R 4 are each independently a hydrogen atom, a C 1 -C 4 alkyl group or an ar(C 1 -C 4 )alkyl group or, when taken together with the adjacent nitrogen atom to which they are attached, represent a nitrogen-containing 5 to 7-membered saturated heterocyclic group optionally having an oxygen atom or an additional nitrogen atom as the hetero atom in addition to the said nitrogen atom and, in case of having the additional nitrogen atom, bearing a hydrogen atom, a C 1 -C 4 alkyl group, an ar(C 1 -C 4 )alkyl group or a phenyl group thereon), ##STR3## is a group of the formula: ##STR4## or the formula: ##STR5## A 1 is a C 2 -C 6 alkylene group and A 2 is a C 2 -C 4 alkylene group, and non-toxic, pharmaceutically acceptable acid addition salts thereof, which have cerebral vasodilating activity and antihypoxic activity.

Claims

exact text as granted — not AI-modified
What is claimed is: 
     
       1. A compound of the formula: ##STR21## wherein R 1  and R 2  are each independently a phenyl, thienyl, furyl or naphthyl group optionally substituted with 1 to 3 substituents selected from the group consisting of halogen, C 1  -C 4  alkyl, C 1  -C 4  alkoxy, nitro, cyano, di(C 1  -C 4 )alkylamino, amino, benzyloxy, hydroxyl, C 1  -C 4  alkylthio, C 1  -C 4  alkylsulfinyl, C 1  -C 4  alkylsulfonyl, C 1  -C 4  alkanoylamino, C 1  -C 4  alkylamino and N-(C 1  -C 4 )alkyl-N-(C 1  -C 4 )alkanoylamino, A 1  is a C 3  -C 6  alkylene group and A 2  is a C 2  -C 4  alkylene group. 
     
     
       2. The compound according to claim 1, wherein R 1  is a phenyl group optionally substituted with 1 or 2 substituents selected from the group consisting of halogen, C 1  -C 4  alkyl, C 1  -C 4  alkoxy, di(C 1  -C 4 )alkylamino, benzyloxy hydroxyl and C 1  -C 4  alkylthio. 
     
     
       3. The compound according to claim 1, wherein R 2  is a phenyl group optionally substituted with C 1  -C 4  alkyl or halogen. 
     
     
       4. The compound according to claim 1, wherein R 2  is a phenyl group. 
     
     
       5. A compound of the formula: ##STR22## wherein R 1  is a phenyl group or a halophenyl group, R 2  is a phenyl group, A 1  is a C 3  -C 6  alkylene group and A 2  is a C 2  -C 4  alkylene group. 
     
     
       6. A compound of the formula: ##STR23## wherein R 1  and R 2  are each independently a phenyl group optionally substituted with 1 to 3 substituents selected from the group consisting of halogen, C 1  -C 4  alkyl, C 1  -C 4  alkoxy, nitro, cyano, di(C 1  -C 4 )alkylamino, amino, benzyloxy, hydroxyl, C 1  -C 4  alkylthio, C 1  -C 4  alkylsulfinyl, C 1  -C 4  alkylsulfonyl, C 1  -C 4  alkanoylamino, C 1  -C 4  alkylamino and N-(C 1  -C 4 )alkyl-N-(C 1  -C 4 )alkanoylamino, A 1  is a C 3  -C 6  alkylene group and A 2  is a C 2  -C 4  alkylene group. 
     
     
       7. A compound of the formula: ##STR24## wherein R 1  is a phenyl group or a halophenyl group and R 2  is a phenyl group, A 1  is a C 3  -C 4  alkylene group and A 2  is a C 2  -C 4  alkylene group. 
     
     
       8. A compound of the formula: ##STR25## wherein R 1  and R 2  are each independently a phenyl group optionally substituted with 1 to 3 substituents selected from the group consisting of halogen, C 1  -C 4  alkyl, C 1  -C 4  alkoxy, nitro, cyano, di(C 1  -C 4 )alkylamino, amino, benzyloxy, hydroxyl, C 1  -C 4  alkylthio, C 1  -C 4  alkylsulfinyl, C 1  -C 4  alkylsulfonyl, C 1  -C 4  alkanoylamino, C 1  -C 4  alkylamino and N-(C 1  -C 4 )alkyl-N-(C 1  -C 4 ) alkanoylamino, A 1  is a C 3  -C 4  alkylene group and A 2  is a C 2  -C 4  alkylene group. 
     
     
       9. A compound of the formula: ##STR26## wherein R 2  is a phenyl, thienyl, furyl or naphthyl group optionally substituted with 1 to 3 substituents selected from the group consisting of halogen, C 1  -C 4  alkyl, C 1  -C 4  alkoxy, nitro, cyano, di(C 1  -C 4 )alkylamino, amino, benzyloxy, hydroxyl, C 1  -C 4  alkylthio, C 1  -C 4  alkylsulfinyl, C 1  -C 4  alkylsulfonyl, C 1  -C 4  alkanoylamino, C 1  -C 4  alkylamino and N-(C 1  -C 4 )alkyl-N-(C 1  -C 4 )alkanoylamino, A 1  is a C 2  -C 6  alkylene group and A 2  is a C 2  -C 4  alkylene group. 
     
     
       10. A compound of the formula: ##STR27## wherein R 2  is a phenyl, thienyl, furyl or naphthyl group optionally substituted with 1 to 3 substituents selected from the group consisting of halogen, C 1  -C 4  alkyl, C 1  -C 4  alkoxy, nitro, cyano, di(C 1  -C 4 )alkylamino, amino, benzyloxy, hydroxyl, C 1  -C 4  alkylthio, C 1  -C 4  alkylsulfinyl, C 1  -C 4  alkylsulfonyl, C 1  -C 4  alkanoylamino, C 1  -C 4  alkylamino and N-(C 1  -C 4 )alkyl-N-(C 1  -C 4 )alkanoylamino, A 1  is a C 2  -C 6  alkylene group and A 2  is a C 2  -C 4  alkylene group. 
     
     
       11. 1-[3-(N,N-Dimethylamino)propoxy]-1,4-diphenylbutane, or a non-toxic, pharmaceutically acceptable acid addition salt thereof. 
     
     
       12. 1-[3-(N,N-Dimethylamino)propoxy]-1-(p-fluorophenyl)-4-phenylbutane, or a non-toxic, pharmaceutically acceptable acid addition salt thereof. 
     
     
       13. 1-[3-(N,N-Dimethylamino)propoxy]-1,5-diphenylpentane, or a non-toxic, pharmaceutically acceptable acid addition salt thereof. 
     
     
       14. 1-[3-(N,N-Dimethylamino)propoxy]-1-thienyl-4-phenylbutane, or a non-toxic, pharmaceutically acceptable acid addition salt thereof. 
     
     
       15. 1-[3-(N,N-Dimethylamino)propoxy]-1-furyl-4-phenylbutane, or a non-toxic, pharmaceutically acceptable acid addition salt thereof.

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